US6391065B1 - UV light absorber composition and method of improving the lightfastness of dyed textiles - Google Patents
UV light absorber composition and method of improving the lightfastness of dyed textiles Download PDFInfo
- Publication number
- US6391065B1 US6391065B1 US08/553,072 US55307295A US6391065B1 US 6391065 B1 US6391065 B1 US 6391065B1 US 55307295 A US55307295 A US 55307295A US 6391065 B1 US6391065 B1 US 6391065B1
- Authority
- US
- United States
- Prior art keywords
- weight
- textiles
- benzotriazole
- light absorber
- light
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related, expires
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 100
- 239000006096 absorbing agent Substances 0.000 title claims abstract description 79
- 239000004753 textile Substances 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title abstract description 14
- 239000012964 benzotriazole Substances 0.000 claims abstract description 19
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 claims description 39
- 239000002904 solvent Substances 0.000 claims description 28
- 239000003995 emulsifying agent Substances 0.000 claims description 23
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 18
- 239000003963 antioxidant agent Substances 0.000 claims description 9
- 230000003078 antioxidant effect Effects 0.000 claims description 9
- 235000006708 antioxidants Nutrition 0.000 claims description 9
- 239000004611 light stabiliser Substances 0.000 claims description 9
- 239000004094 surface-active agent Substances 0.000 claims description 9
- 229920002994 synthetic fiber Polymers 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000004758 synthetic textile Substances 0.000 claims 5
- 150000001565 benzotriazoles Chemical class 0.000 claims 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 9
- 239000012965 benzophenone Substances 0.000 abstract description 5
- 150000003918 triazines Chemical class 0.000 abstract description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 39
- 238000003756 stirring Methods 0.000 description 30
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 25
- 239000000975 dye Substances 0.000 description 20
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 13
- 239000000839 emulsion Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 12
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000012875 nonionic emulsifier Substances 0.000 description 6
- 229960002903 benzyl benzoate Drugs 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- YCZJVRCZIPDYHH-UHFFFAOYSA-N ditridecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCCCC YCZJVRCZIPDYHH-UHFFFAOYSA-N 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 238000009991 scouring Methods 0.000 description 4
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 4
- 239000008399 tap water Substances 0.000 description 4
- 235000020679 tap water Nutrition 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 4
- XYXJKPCGSGVSBO-UHFFFAOYSA-N 1,3,5-tris[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CN1C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C1=O XYXJKPCGSGVSBO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 3
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 230000000007 visual effect Effects 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical group C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002314 glycerols Chemical class 0.000 description 2
- NZYMWGXNIUZYRC-UHFFFAOYSA-N hexadecyl 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NZYMWGXNIUZYRC-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000009974 package dyeing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- BYLSIPUARIZAHZ-UHFFFAOYSA-N 2,4,6-tris(1-phenylethyl)phenol Chemical compound C=1C(C(C)C=2C=CC=CC=2)=C(O)C(C(C)C=2C=CC=CC=2)=CC=1C(C)C1=CC=CC=C1 BYLSIPUARIZAHZ-UHFFFAOYSA-N 0.000 description 1
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
- RKKNJQVSNIZPFI-UHFFFAOYSA-N 3,5-dibutyl-4-hydroxybenzoic acid Chemical compound CCCCC1=CC(C(O)=O)=CC(CCCC)=C1O RKKNJQVSNIZPFI-UHFFFAOYSA-N 0.000 description 1
- SIXWIUJQBBANGK-UHFFFAOYSA-N 4-(4-fluorophenyl)-1h-pyrazol-5-amine Chemical compound N1N=CC(C=2C=CC(F)=CC=2)=C1N SIXWIUJQBBANGK-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001356 alkyl thiols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 238000013142 basic testing Methods 0.000 description 1
- 150000008366 benzophenones Chemical group 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- SCKHCCSZFPSHGR-UHFFFAOYSA-N cyanophos Chemical compound COP(=S)(OC)OC1=CC=C(C#N)C=C1 SCKHCCSZFPSHGR-UHFFFAOYSA-N 0.000 description 1
- -1 defoamers Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002303 glucose derivatives Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000009981 jet dyeing Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000002931 p-cresols Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229940124543 ultraviolet light absorber Drugs 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000009976 warp beam dyeing Methods 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/02—After-treatment
- D06P5/04—After-treatment with organic compounds
- D06P5/06—After-treatment with organic compounds containing nitrogen
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/0024—Dyeing and bleaching in one process
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/60—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
- D06P1/613—Polyethers without nitrogen
- D06P1/6131—Addition products of hydroxyl groups-containing compounds with oxiranes
- D06P1/6133—Addition products of hydroxyl groups-containing compounds with oxiranes from araliphatic or aliphatic alcohols
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/6426—Heterocyclic compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/645—Aliphatic, araliphatic or cycloaliphatic compounds containing amino groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65112—Compounds containing aldehyde or ketone groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/90—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof
- D06P1/92—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
- D06P1/928—Solvents other than hydrocarbons
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
Definitions
- This invention relates to an ultraviolet light absorber composition which is readily diluted in, and applied from, a water-based textile dye bath to improve the lightfastness, or fade-resistance, of a dyed textile material, for example, knitted or woven fabric.
- the invention is based upon the synergistic combination of a UV light absorber and a suitable solvent.
- a solvent-soluble emulsifier surfactant
- the emulsifier may also be applicable when using a water miscible solvent to improve the dilutability of the UV light absorber.
- the water miscible solvent dissolves in the water-based dye bath to form an extremely fine dispersion of UV light absorber.
- the dyed textiles treatable by this invention generally include synthetic fibers, such as polyester and nylon (polyamide).
- the invention is applied to disperse-dyed polyester fabric used in automobile interiors, for example, in seat upholstery, door and head liners, and carpeting, to improve the fade-resistance of the fabric.
- the absorber/stabilizer agents In order to apply UV light absorbers and other light stabilizers to textiles after the textile fiber has been formed rather than in the melt-extrusion stage, the absorber/stabilizer agents must be dilutable in water to be effectively used in conventional textile dyeing and processing machinery. Standard UV light absorber and light stabilizer compounds, however, have little or no solubility in water, and must therefore be wet-milled. Wet-milling is a process of mechanically, grinding down the absorber/stabilizer agents in water in small media mills, e.g., sand mills or ball mills, together with various dispersing and wetting agents, processing aids, and the like. Other ingredients such as leveling agents, particle recrystallization inhibitors, preservatives, defoamers, and thickeners are also generally required.
- the wet-mill process suffers from numerous drawbacks and limitations. A great deal of time and energy is required to physically break down the absorber/stabilizer agents. Typically, the particle size must be less than two microns mean diameter in order to produce a suitable aqueous dispersion that is both storage stable, and will not filter out when passed through many layers of fiber or fabric in conventional dyeing machinery, such as in package or beam dyeing machines.
- the wet-mill process may take as long as several days for a single preparation.
- the composition includes from about 5-75% by weight of an ultraviolet light absorbing agent selected from the group consisting of benzotriazole, benzophenone, and phenol substituted triazine; and from about 25-95% by weight of an organic solvent suitable for dissolving the ultraviolet light absorbing agent.
- the ultraviolet light absorbing agent is applied to the textiles in a concentration sufficient to result in an add-on in the range of between 0.4-4.0% by weight of the textiles when dry.
- the organic solvent is a water miscible solvent.
- the organic solvent is a water immiscible solvent
- the composition further includes from about 2-25% by weight of a surfactant.
- the surfactant is nonylphenoxy-polypropyleneoxy-polyethyleneoxy-ethanol.
- the composition includes from about 2-25% by weight of a surfactant in a water miscible solvent.
- the composition includes an additional light stabilizer selected from the group including hindered amines and organo-copper complexes.
- the composition includes an anti-oxidant.
- the UV light absorbing agent is 2-(2-hydroxy-5-tert-octylphenyl)-benzotriazole.
- the organic solvent is N-methyl-pyrrolidone.
- the ultraviolet light absorbing agent is applied to the textiles in a concentration sufficient to result in an add-on of approximately 1.0% by weight of the textiles when dry.
- a UV light absorber composition for improving the lightfastness of dyed textiles includes from about 10-30% by weight of 2-(2-hydroxy-5-tert-octylphenyl)-benzotriazole, from about 55-85% by weight of N-methyl-pyrrolidone solvent, and from about 5-15% by weight of nonylphenoxy-polypropyleneoxy-polyethyleneoxy-ethanol.
- the benzotriazole is applied to the textiles in a concentration sufficient to result in an add-on in the range of between 0.4-4.0% by weight of the textiles when dry.
- An embodiment of the method according to the invention comprises the steps of formulating a UV light absorbing composition.
- the composition includes from about 5-75% by weight of an ultraviolet light absorbing agent selected from the group consisting of benzotriazole, benzophenone, and phenol substituted triazine; and from about 25-95% by weight of an organic solvent suitable for dissolving the ultraviolet light absorbing agent.
- the ultraviolet light absorbing agent is applied to the textiles in a concentration sufficient to result in an add-on in the range of between 0.4-4.0% by weight of the textiles when dry.
- the method further includes adding the above composition and textiles to be treated into a water-based dye bath.
- the method includes the step of scouring the textiles with a scouring agent prior to adding the textiles to the water-based dye bath.
- the method includes the step of heating the textiles after scouring to a temperature in the range of about 60° C. to about 80° C. at a rate of 2° C. per minute, and prior to adding the textiles to the dye bath.
- the method includes the step of drying the textiles prior to adding the textiles to the dye bath.
- the step of formulating a UV light absorbing composition includes the step of adjusting the pH of the composition to between about 4.0 and 5.0 prior to adding the composition to the dye bath.
- the step of formulating a UV light absorbing composition includes the step of adjusting the pH of the composition to about 4.8 prior to adding the composition to the dye bath.
- the UV light absorber composition of the present invention is a non-aqueous composition usable in water-based dye baths for enhancing the lightfastness of dyed textiles.
- the composition includes a mixture of at least a UV light absorbing agent and a suitable solvent.
- the composition further includes an emulsifier such that the composition spontaneously forms an emulsion when diluted in water.
- An emulsifier may also be used with water miscible solvents to improve the dilutability of the composition in the dye bath.
- the UV light absorbing agent is chosen from one or more of the following classes; benzotriazole, benzophenone, and phenol substituted triazine. Preferably, these agents are used individually, but may be used in combination to obtain various mixtures of active UV light absorbing ingredients.
- benzotriazole UV light absorbing agent is 2-(2-Hydroxy-5-tert-octylphenyl)-benzotriazole, CAS Reg. No. 3147-75-9, which is commercially available as “Cyasorb UV-5411” from Cytec Industries. Examples of suitable benzophenones and phenol substituted triazines are disclosed in U.S. Pat. Nos. 4,826,978 and 4,964,871. A number of other commercially available UV light absorbing agents are set forth in the Examples provided below.
- the solvent may be any suitable water miscible or immiscible organic solution, or mixture of water miscible and immiscible solutions, capable of dissolving the active UV light absorbing agent of the composition.
- the solvent For compositions using a water immiscible or partially immiscible solvent, the solvent must further be capable of dissolving the added emulsifier.
- a number of applicable solvents are provided in the Examples below.
- the solvent can function as a carrier or diffusion accelerator for the UV light absorbing agent into hydrophobic fibers, such as polyester. Solvents chosen from the class of plasticizer esters are especially suitable for this purpose.
- the emulsifier is preferably chosen from the group including alkanolamides, ethylene oxide/propylene oxide block polymers, alkylphenol ethoxylates, dialkylphenol ethoxylates, styrenated-phenol ethoxylates, ethoxylated alcohols, ethoxylated fatty acids (esters), ethoxylated amines, ethoxylated amides, glycerol esters, ethoxylated glycerol esters, sorbitan esters, ethoxylated sorbitan esters, sucrose and glucose esters, alkyl polyglycosides, ethoxylated alkyl thiols, ethoxylated thio-ethers.
- ethoxylated or “ethoxylates”
- ethoxylated/propoxylated variations could also be used.
- a listing of suitable commercially available emulsifiers is provided in McCutcheon's Emulsifiers and Detergents 1994—North American and International Editions (McCutcheon Division, MC Publishing, 175 Rock Road, Glen Rock, N.J. 07452).
- the emulsifier selected must be soluble in the particular water miscible or immiscible solvent used. Generally, to be soluble in such solvents, the hydrophilic-lipophilic balance (HLB) of the emulsifier should be less than about 13. The most preferred nonionic emulsifiers should have HLBs of about 5 to 11.
- ionic emulsifiers may be used in the present composition, provided they are sufficiently soluble in the solvent.
- the ionic emulsifier used should also be anionic or possibly amphoteric. Cationic emulsifiers may not be compatible in the final dye baths where the UV light absorbing composition would commonly be applied.
- the UV light absorber composition includes approximately 5-75% of organic UV light absorbing agent; approximately 25-95% of organic solvent; and for water immiscible or partially immiscible solvents, approximately 2-25% of an emulsifier which is soluble in the above mixture.
- the solvent must therefore be capable of dissolving at least 5% of a UV light absorbing agent, and at least 2% of an emulsifier when applicable.
- the UV light absorbing agent of the composition is combined with other classes of light stabilizers, such as hindered amines and organo-copper complexes; and/or various anti-oxidant compounds to achieve synergistic lightfastness and fiber protection effects.
- a hindered amine is Bis(1,2,2,6,6-pentamethyl-4-piperidinyl)sebacate, commercially available as “Tinuvin 292” from Ciba-Geigy.
- suitable organo-copper complexes are described in U.S. Pat. Nos. 4,990,164 and 5,076,808.
- One suitable anti-oxidant compound is “Cyanox 2777” from Cytec Industries.
- the present UV light absorbing composition is applicable in beam and package dyeing of textiles, and dyeing operations where the dye bath liquor is stationary and the fabric is moving, such as in jet dyeing and continuous dyeing machines.
- compositions formulated according to the present invention are compositions formulated according to the present invention. Information appearing in brackets beside selected Examples relates to the testing ID of the particular sample composition as referenced in Tables 1-4.
- a solution of 5 g D-Limonene (CAS No. 5989-27-5) and 5 g “Cyasorb UV-5411” was mixed and heated. The mixture formed a clear yellow solution down to 55° C. An additional 5 g D-Limonene was then added. The mixture formed a clear solution down to 45° C. To this was added 5 g of a nonionic emulsifier, nonylphenoxy-polypropyleneoxy-polyethyleneoxy-ethanol (CAS Reg. No. 68891-11-2), commercially available as “Tergitol D-683” from Union Carbide. The mixture formed a clear solution down to 40° C., but was an opaque off-white “slush” at room temperature. The resulting solution was relatively dispersible in warm water (45-50° C.) with stirring.
- the mixture formed a clear yellow solution which resulted in an opaque white emulsion when diluted in water.
- the mixture formed a clear yellow solution which resulted in an opaque white emulsion when diluted in water.
- Example 10 Into the solution of Example 10 including 81% by weight “Jayflex DIOP” plasticizer and 9% by weight “Cyasorb UV-5411”, slowly added 10% by weight “Tergitol D-683” emulsifier while stirring. The resulting solution forms an opaque white emulsion when diluted in water.
- Example 12 Into the solution of Example 12 including 67.5% by weight N-methyl pyrrolidone and 22.5% by weight “Cyasorb UV-5411”, slowly added 10% by weight of “Tergitol D-683” emulsifier. The solution formed a cloudy, pearlescent emulsion when diluted in water.
- Each of the tested UV light absorber compositions was applied to a 10 g sample of grey-dyed, 100% automotive polyester yarn (knitted into a tube) in a water-based mock dye bath with a liquor ratio of 10:1. As indicated in Table 1, the concentration of each composition contained in the respective dye baths was adjusted such that 1% of active UV light absorbing agent to dry weight of yarn was used. Although not specifically tested, other suitable proportions ranging from about 0.4% to about 4.0% active UV light absorbing agent to dry weight of yarn are also applicable for achieving enhanced lightfastness of the yarn.
- the yarn samples were subjected to the following test procedures using an “Ahiba Polymat” laboratory dyeing machine manufactured by Ahiba:
- experimental VP 2305-B of the present invention was comparable to “Sandolite LP” for exhaustion properties, and slightly better than the “Sandolite LP” for automotive lightfastness.
- the VP 2305-B composition includes the following:
- N-methyl-pyrrolidone CAS Reg. No. 872-50-4
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- Engineering & Computer Science (AREA)
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- Cosmetics (AREA)
- Coloring (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
TABLE 1 |
FORMULATIONS (Grams/100 grams) |
Mix Number |
Product | Activity (%) | A | B | C | D | E | F | G | H |
VP 2305-A | 9.0 | 1.1 | — | — | — | — | — | — | — |
VP 2305-B | 22.5 | — | 0.44 | — | — | — | — | — | — |
VP 2305-C | 19.8 | — | — | 0.51 | — | — | — | — | — |
VP 2017-C | 10.0 | — | — | — | 1.00 | — | — | — | — |
VP 2018-D | 13.0 | — | — | — | — | 0.77 | — | — | — |
VP 2021-A | 18.0 | — | — | — | — | — | 0.56 | — | — |
VP 2021-B | 18.0 | — | — | — | — | — | — | 0.56 | |
Sandolite LP | 25.0 | — | — | — | — | — | — | — | 0.40 |
TABLE 2 |
UV ABSORBER |
TEST METHOD CONDITIONS |
Test Method | GM 9125-P/SAE J 1885 | ||
Exposure Device | Ci-65 #4 | ||
Serial Number | CB-1431 | ||
Light Source | Controlled Irradiance Xenon Arc | ||
Filter Type | Quartz Inner, Borosilicate S Outer | ||
Irradiance Level | .55 W/m2 @ 340 nm | ||
Elapsed Exposure | 300.8 kJ/m2 Hours | ||
Cam Number 60 | 3.5 Hours Light/1 Hour Dark | ||
Black Panel Temperature | 89 ± 3° C. Light 38 ± 2° C. Dark | ||
Dry Bulb Temperature | 62 ± 2° C. Light 38 ± 2° C. Dark | ||
Relative Humidity | 50 ± 5% Light 95 ± 5% Dark | ||
Spray Water Type | None | ||
Spray Nozzle | N/A | ||
Specimen Rotation | None | ||
TABLE 3 |
EXHAUSTION OBSERVATION |
Visual Observation |
Product | Before | After |
VP 2305-A | White opaque liquid | Cloudy with brown tint |
VP 2305-B | Pearlescent, white opaque | Clear water white |
liquid | ||
VP 2305-C | Hazy, white opaque liquid | Clear water white |
VP 2017-C | Hazy, white opaque liquid | Hazy liquid with brown tint |
VP 2018-D | Hazy liquid | Hazy liquid with brown tint |
VP 2021-A | Hazy, white opaque liquid | Slightly hazy liquid |
with particles | ||
VP 2021-B | Hazy, white opaque liquid | Hazy liquid with blue tint |
with particles | ||
Sandolite LP | White opaque liquid | Clear water white |
UV ABSORBERS — COLORMETRIC DATA |
Specimen | Original | Present | Delta | AATCC Gray Scale | Visual |
Number | L* | a* | b* | L* | a* | b* | L* | a* | b* | E* | Color Change | Ranking |
Control | 63.98 | 3.70 | −2.00 | 67.80 | 4.16 | −1.90 | 3.82 | 0.46 | 0.10 | 3.85 | 2.5 | 6 |
(No UV Absorber) | ||||||||||||
VP 2305-A | 63.98 | 3.70 | −2.00 | 65.38 | 4.25 | 0.00 | 1.40 | 0.55 | 2.00 | 2.50 | 2.5 | 7 |
VP 2305-B | 62.98 | 4.08 | 0.03 | 66.59 | 4.08 | −0.06 | 3.61 | 0.00 | −0.09 | 3.61 | 3.5 | 1 |
VP 2305-C | 63.06 | 4.01 | 0.04 | 70.38 | 2.35 | 0.62 | 7.32 | −1.66 | 0.58 | 7.53 | 3.0 | 3 |
VP 2017-C | 64.95 | 3.29 | −1.62 | 68.62 | 4.02 | −0.61 | 3.67 | 0.73 | 1.01 | 3.88 | 2.0 | 8 |
VP 2018-D | 64.52 | 3.87 | −1.14 | 65.75 | 4.31 | −0.56 | 1.23 | 0.44 | 0.58 | 1.43 | 2.5 | 9 |
VP 2021-A | 62.92 | 4.07 | −0.51 | 66.68 | 4.13 | −0.35 | 3.76 | 0.06 | 0.16 | 3.76 | 4.0 | 5 |
VP 2021-B | 63.28 | 4.41 | −0.28 | 64.47 | 3.27 | 1.39 | 1.19 | −0.87 | 1.67 | 2.23 | 2.5 | 4 |
Sandolite LP | 62.41 | 3.57 | 1.10 | 67.23 | 4.76 | −0.76 | 4.82 | 1.19 | −1.86 | 5.30 | 3.5 | 2 |
Claims (6)
Priority Applications (2)
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US08/553,072 US6391065B1 (en) | 1995-11-03 | 1995-11-03 | UV light absorber composition and method of improving the lightfastness of dyed textiles |
EP96307615A EP0774539A3 (en) | 1995-11-03 | 1996-10-22 | UV light absorber composition and method of improving the lightfastness of dyed textiles |
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US08/553,072 US6391065B1 (en) | 1995-11-03 | 1995-11-03 | UV light absorber composition and method of improving the lightfastness of dyed textiles |
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US20040082694A1 (en) * | 2001-02-21 | 2004-04-29 | Kenzo Kubo | Polyphenylene sulfide member and its manufacturing method |
US20050022313A1 (en) * | 2003-07-08 | 2005-02-03 | Scheidler Karl J. | Methods and compositions for improving light-fade resistance and soil repellency of textiles and leathers |
US20060231799A1 (en) * | 2005-04-19 | 2006-10-19 | R.T. Vanderbilt Company, Inc. | Topical polyurethane foam oxidative photooxidative stabilizer |
US20070032156A1 (en) * | 2005-06-24 | 2007-02-08 | Paola Bianco | Microfibrous non-woven chamois fabric having a high light fastness and process for its preparation |
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US20040082694A1 (en) * | 2001-02-21 | 2004-04-29 | Kenzo Kubo | Polyphenylene sulfide member and its manufacturing method |
US8097048B2 (en) * | 2001-02-21 | 2012-01-17 | Toray Industries, Inc. | Polyphenylene sulfide member and method for producing the same |
US7824566B2 (en) | 2003-07-08 | 2010-11-02 | Scheidler Karl J | Methods and compositions for improving light-fade resistance and soil repellency of textiles and leathers |
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JPWO2006013703A1 (en) * | 2004-08-04 | 2008-05-01 | 株式会社Adeka | Light stabilizer emulsified composition and water-based coating agent composition containing the same |
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US20070032156A1 (en) * | 2005-06-24 | 2007-02-08 | Paola Bianco | Microfibrous non-woven chamois fabric having a high light fastness and process for its preparation |
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US20080207804A1 (en) * | 2007-02-26 | 2008-08-28 | Gelbin Michael E | Stabilization of polymers with styrenated-p-cresols |
US8512421B2 (en) | 2011-09-19 | 2013-08-20 | Everlight Chemical Industrial Corporation | Polyurethane derivatives, composition thereof and dye additives comprising the polyurethane derivatives |
US20180362800A1 (en) * | 2017-06-16 | 2018-12-20 | Ergo-Industrial Seating Systems Inc. | Protective graft coating for application onto polyurethane for chemical resistance, stain resistance, abrasion resistance and u.v. resistance |
US11492510B2 (en) * | 2017-06-16 | 2022-11-08 | Ergocentric Inc. | Protective graft coating for application onto polyurethane for chemical resistance, stain resistance, abrasion resistance and U.V. resistance |
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Also Published As
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EP0774539A2 (en) | 1997-05-21 |
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